Head of Engineering
About Wonderschool
Wonderschool builds software and systems that help businesses operate, grow, and generate revenue. We started in childcare and are expanding into adjacent verticals including healthcare, microschools, and other service-based businesses. Our platform combines marketplace, SaaS, and government infrastructure.
We are a Series B company backed by Andreessen Horowitz, Goldman Sachs, Long Journey Ventures, and First Round Capital. The business is cash flow positive and expanding.
A core part of our strategy is using AI systems to increase speed and leverage across the company. We have a dedicated Head of AI Agent Systems role focused on building that capability. The Head of Engineering is responsible for building the high-performing engineering organization that can ship reliable, scalable products and fully leverage these systems.
Position Summary
The Head of Engineering owns product delivery, engineering execution, and team performance.
This role is responsible for ensuring the engineering team consistently ships high-quality, revenue-driving product quickly and reliably. It is a hands-on leadership role: you will manage the team, drive execution, improve development processes, and partner closely with Product and the Head of AI Agent Systems to increase velocity.
This role reports directly to the CEO.
Responsibilities
Own Engineering Execution and Delivery
Ensure the team consistently ships high-quality product on time
Reduce time from idea to production for core features
Drive accountability for delivery across the team
Prioritize and ship features tied to revenue quickly
Build and Lead a High-Performance Engineering Team
Manage, coach, and develop engineers
Hire strong engineers and raise the bar over time
Set a high performance standard and enforce it
Address underperformance quickly and directly
Improve Development Velocity and Quality
Improve engineering processes to increase speed without sacrificing quality
Ensure code quality, testing, and reliability standards are maintained
Partner with the Head of AI Agent Systems to integrate AI-driven workflows into the development process
Ensure engineers adopt tools and systems that increase output
Own Architecture and Technical Direction
Make and enforce key architectural decisions
Ensure systems are scalable, maintainable, and aligned with product needs
Drive simplification and reduce technical debt where it slows the business
Partner with Product and Business Teams
Work closely with the Head of Product to translate priorities into shipped product
Ensure alignment between product requirements and engineering execution
Support GTM and operations by delivering the systems needed to drive revenue
Drive Business Impact
Ensure engineering output directly supports revenue growth
Improve the speed of shipping features that impact conversion, onboarding, and usage
Balance speed and reliability to support long-term growth
What Success Looks Like (6-12 Months)
Engineering consistently ships high-quality product on time
Time from idea to production is significantly reduced
The team is high-performing with clear accountability
Engineering output is clearly tied to revenue and product usage
AI systems are fully integrated into engineering workflows
Required Qualifications
Strong engineering background with experience building and shipping production systems
Experience managing and scaling engineering teams
Track record of delivering product quickly in a high-growth environment
Strong technical judgment and ability to make architectural decisions
Experience working closely with product and business teams
Preferred Qualifications
Experience at a high-growth startup
Experience improving engineering velocity and processes
Experience integrating AI or automation into development workflows
Background as a founder or early-stage engineer
What We Are Looking For
Someone who builds high-performing teams, not just systems
Someone who drives execution and holds people accountable
Someone who balances speed and quality effectively
Someone who partners well with product and leadership
Someone who is comfortable being hands-on when needed
Compensation and Benefits
Compensation is competitive and commensurate with experience. This role is eligible for equity.
Wonderschool offers a competitive benefits package, including:
Health benefits with up to 100% coverage for employee premiums and up to 80% for dependents
Wifi and employee wellness stipends
Flexible PTO, paid holidays, and mental wellness days
Competitive parental leave (eligible after 6 months of employment)
Location
In-person, 5-6 days a week in our office in Rincon Hill, San Francisco.
Wonderschool is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and talent.